Managing multiple Macs?

I'm not even sure where to begin with this one, but I have an hallucination that there is some combination of software and admin settings that would allow me to perform simultaneous upgrades system wide to the 18 odd Macs that I have in my office. As it is, I have to go machine to machine, downloading upgrade install files from my main desktop, or using an upgrade DVD.
I'm a long standing Mac user with 25 years of experience, but I'm not a network genius... I usually just come to the discussion board and poke around until I find someone with a similar problem and see what they do.
Is there a way to configure all of my Macs so that I can boot them all up and send upgrade commands/data from one machine? My office is structured so that our server's only purpose is to access our medical office management software (MacPractice) which contains charting, patient info, scheduling and billing info... all else is done at each terminal with it's own copy of Safari and iWorks, with 4 networked printers available.
I'm thinking there is some kind of Server Admin 101 that would help a nitwit like me, so I don't spend an entire weekend babysitting 18 different system upgrades. Thanks for any direction someone can provide!

Thanks, that's probably what I'm looking for (Remote Desktop).... looks like a $500 item to manage all my computers, plus a bit of a learning curve. Have to decide if that's worth it, considering I only really have this time consuming upgrade business once a year or so, but that would probably be the way to go, especially if I was doing a lot more micro-managing and distribution of files.
Thanks for the prompt help, I knew someone would know what they're talking about round these parts!

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